Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity

Bioorg Med Chem Lett. 2017 Apr 1;27(7):1525-1529. doi: 10.1016/j.bmcl.2017.02.040. Epub 2017 Feb 21.

Abstract

Using various chromatographic methods, five new sesquiterpene derivatives named smenohaimiens A-E (1-5) and five known, 19-hydroxy-polyfibrospongol B (6), ilimaquinone (7), dictyoceratin C (8), polyfibrospongol A (9), and polyfibrospongol B (10) were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were assigned by 1D, 2D NMR spectroscopic analysis, HR ESI MS, and calculations of the electron circular dichroism spectra. All compounds were evaluated for the inhibitory activity against NO production in lipopolysaccharide-stimulated in BV2 microglia cells. As the results, compound 7 significantly inhibited NO production with the IC50 value of 10.40±1.28µM. The remaining compounds showed moderate inhibitory NO production activities with IC50 values ranging from 24.37 to 30.43µM.

Keywords: Anti-inflammation; Sesquiterpene derivative; Smenohaimiens A–E; Smenospongia cerebriformis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Cell Line
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Porifera / chemistry*
  • Quinones / chemistry
  • Quinones / isolation & purification
  • Quinones / pharmacology
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Stereoisomerism
  • omega-N-Methylarginine / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Quinones
  • Sesquiterpenes
  • omega-N-Methylarginine
  • Nitric Oxide
  • ilimaquinone